The solvolysis of 4-phenylbutyl p-nitrobenzenesulfonate in 2,2,2-trifluoroethanol and 1,1,1,3,3,3-Hexafluoropropan-2-ol

Abstract

Kinetic and product studies show that 4-phenylbutyl p-nitrobenzenesulfonate solvolyses predominately via the n-route in buffered 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoropropan-2-ol; the extent of cyclization in the two solvents is 69 and 99.5%, respectively. In buffered acetic acid, only 3.6% cyclized product is obtained. The advantage of the use of the two fluorinated alcohols for inducing π-participation during solvolysis is thus demonstrated.